首页|Ni-Cata lyzed Enantioselective Difunctionalization of Alkynes to Azepine Derivatives Bearing a Quaternary Center and an Unprotected Imine

Ni-Cata lyzed Enantioselective Difunctionalization of Alkynes to Azepine Derivatives Bearing a Quaternary Center and an Unprotected Imine

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The azepine ring is a prominent structural scaffold in biologically significant molecules.In this study,we present a Ni(Ⅱ)-catalyzed asymmetric difunctionalization of alkynes,involving intermolecular regioselective arylation and intramolecular nitrile addition,ena-bling the synthesis of enantioenriched azepine derivatives.This reaction simultaneously installs an all-carbon quaternary stereocenter and introduces an unprotected imine functionality,showing great promise for subsequent transformations.The reaction exhibits good tolerance toward various functional groups,resulting in high yields and enantioselectivities.The synthetic utility of this meth-odology is further demonstrated through gram-scale synthesis and product derivatization.This research offers an efficient approach to the synthesis of seven-membered nitrogen heterocycles.

NickelAsymmetric catalysisN-HeterocyclesAlkyne functionalizationQuaternary centers

Jian Long、Zhiwu Lu、Xiao-Lin Li、Peng Xue、Wen-Bo Liu

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Engineering Research Center of Organosilicon Compounds & Materials(Ministry of Education)and College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,Hubei 430072,China

NSFCNSFCNSFC国家重点研发计划Largescale Instrument and Equipment Sharing Foundation of Wuhan University中国博士后科学基金Core Research Facilities of CCMS(WHU)are acknowledged for access to analytic equipment

2222211121971198223712152022YFA15029022022M712458

2024

10.1002/cjoc.202300647

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(8)
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